C8 aromatic hydrocarbon separation



Aug. 19, 1958 N. FRAGEN C8 AROMATIC HYDROCARBON SEPARATION Filed July 26. 1954 2 Sheets-Sheet 1 m WM.

INVENTOR Naf/mn Fragen Wm; .@@M

ATTORNEY Aug. 19, 1958 N. FRAGEN C8 AROMATIC HYDRocARBoN SEPARATION 2 Sheets-Sheet 2 Filed July 26. 1954 NNN mw LGS:

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INVENTOR.

Naf/Ian Fragen .WM

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ATTORNEY xylene and p-xylene and high purity ethylbenzene.

, '2,848,518 Patented Aug. 19, 1958 ice 2,s4s,s1s

o8 ARoMArIC HYDRoCARBoN sEPAnArroN Nathan Fragen, Hammond, Ind., assignor to Standard Oil Company, Chicago, lll., a corporation of indiana Application .luly 26, 1954, Serial No. 445,597

4 Claims. (Cl. 26o-674) This invention relates to the separation of a mixture of C8 aromatic hydrocarbons into the individual xylene isomers and ethylbenzene. More particularly the invention relates to the treatment of a mixture of C8 aromatic hydrocarbons to recover essentially pure o-xylene, mxylene, p-xylene, ethylbenzene and some l,3-dimethyl-5- ethylbenzene.

Presently there exists a very large demand for high purity o-xylene for the production of phthalic anhydride; high purity p-xylene for the production of synthetic resins; and ethylbenzene for the preparation of styrene polymers. One ethylbenzene derivative, 1,3-dimethyl-5-ethylbenzene, i. e., 1,3,5-ethylxylene, is of considerable interest as a source of styrene-type resin having a softening point above the boilingpoint of water. Presently the chief use for m-xylene is as a solvent.

Distillates obtained from the catalytic reforming, in the presence of hydrogen, of petroleum naphthas contain very large amounts ofthe C8 aromatic hydrocarbons which exist in about the thermodynamic equilibrium distribution. Today it is possible to obtain a C8 aromatic hydrocarbon fraction from petroleum sources, which fraction contains essentially nol non-aromatic hydrocarbon constituents.

It is an extremely complex problem to separate a natural mixture of C8 aromatic hydrocarbons into their individual constituents. Usually the xylene fraction is superfractionated to produce a bottoms product containing about 80% of the o-xylene. The overhead which contains m-xylene, p-xylene, ethylbenzene and some oxylene is then subjected to crystallization in order .to Separate out high purity p-xylene. Unfortunately, this technique results in the production of a fraction containing substantially all the m-xylene and 'the ethylbenzene. This m-xylene-ethylbenzene fraction is not readily separable except by selective alkylation of the m-xylene` The problem of recovery of the o-xylene by fractionation and the p-xylene by crystallization is considerably. simplied if m-xylene is removed from the xylene feed before the crystallization operation.

An object of the invention is the separation of a C8 aromatic hydrocarbon mixture into the various C8 isomers. Another object of the invention is the separation of a C8 aromatic hydrocarbon mixture under conditions to maximize the recovery of essentially pure o- Still another object is a process for the separation of a mixture containing only the xylene isomers and ethylbenzene into essentially pure vo-xylene, p-xylene, m-xylene, high purity ethylbenzene and l,3-dimethyl-5-ethylbenzene under conditions wherein degradation of o-xylene and p-xylene is substantially eliminated.

Figure l shows an illustrative embodiment of the process wherein an ethylbenzene, o-xylene, and p-xylene stream is distilled before separation by crystallization.

Figure 2 shows an illustrative embodiment of the process wherein an ethylbenzene, o-xylene, and p-xylene 2 stream undergoes crystallization separation before distillative separation.

The process of this invention comprises: A feed, consisting essentially of a mixture of all the xylene isomers and ethylbenzene is contacted with HF-BF3 treating agent under conditions of temperature, time, and BF3 usage such that the m-xylene and some of the ethylbenzene (as diethylbenzene and ethylxylene) is extracted into the HF-BF3 acid phase; the ratnate phase contains substantially all the o-xylene and p-xylene and unconverted ethylbenzene. The railinate phase is freed of HF and BF3 and is then distilled to obtain a bottoms product consisting of high purity o-xylene and a fraction containing the C8 aromatic hydrocarbons not removed in the bottoms product. This fraction is chilled to obtain only crystals of p-xylene and a mother liquor. The mother liquor is distilled to obtain a high purity ethylbenzene fraction and a mixture of o-xylene, p-xylene, and ethylbenzene. The HF-BFs acid phase is then contacted under conditions of time and temperature so controlled that essentially all the ethylbenzenes interact with xylene to produce l,3-dimethyl-5-ethylbenzene and benzene as essentially the only interaction products and the o-xylene and p-xylene present (if any) are isomerized to m-xylene; these are recovered from the acid phase.

Another process subjects the ranate to crystallization at a temperature such that crystals of both o-xylene and p-xylene are formed; these crystals are separated from a mother liquor. The mixture of crystals is recrystallized at a temperature such that only essentially pure p-xylene crystals are formed; these are separated from a mother liquor consisting essentially of a eutectic mixture of o-xylene and p-xylene. The eutectic mixture is distilled to recover an essentially pure o-xylene product. The mother liquor from the lirst crystallization is distilled to recover a high purity ethylbenzene product.

The invention is described in conjunction with the drawings which drawings form a part of this specification. It is to be understood that the drawings are schematic in nature and that many items of process` equipment have been omitted as these may be readily added by one skilled in the art.

In Figure l, feed from source 10 is passed by way of line 11 into line 12. The feed to the process is a mixture of o-xylene, p-xylene, m-xylene, and ethylbenzene either a natural mixture or one made up by fractions from. various conversion processes. The xylene mixture is essentially pure with respect to non-aromatic hydrocarbon constituents, i. e., contains essentially no nonaromatic hydrocarbons boiling in the xylene boiling range of 139-144 C. It is desirable to dilute the xylene feed with a low boiling hydrocarbon which is readily separable from the xylenes by distillation. Examples of suitable hydrocarbons are pentane and hexane; or a higher boiling hydrocarbon may be used as a diluent, although this is not preferred because of the increased diculty of separation by fractional distillation. The total feed preferably consists of about 50 volume percent of the C3 aromatic hydrocarbons and the remainder diluent nonaromatic hydrocarbons. In this illustration, the feed consists of an essentially pure xylene fraction derived by solvent extraction of a hydroformate. The xylene fraction contains, on a volume basis, o-xylene, 21.1 volumes; m-xylene, 36.8 volumes; p-xylene, 15.8 volumes; and ethylbenzene, 26.3 volumes. The feed has been diluted with pentane from source 13 to have a paranic content of about 50 volume percent. The pentane is passed by way of line 14 in line 12. The combined stream is passed into extractor 15.

Extractor 15 is a conventional countercurrent contact-l ing tower which may be provided with any of the various conventional methods for obtaining ecient contacting be? tween two immiscible liquids. Extractor 15 may be operated at constant temperature from top to bottom or by the use of heat exchanger means 16, 17, and 18, the temperature may be varied over the height of the tower. A substantiallyfconstant temperature is maintained throughout the tower at C.

The temperature and-time of contactingbetween the C8 aromatic hydrocarbons and the HF-BF3 treating agent must be so controlled that essentially no isomerization of the o-xylene and p-xylene takes place. In general, a suitable temperature of operation is between about 40 C. and +30 C. At these temperatures, the time of contacting may be between about 2 minutes and 30 minutes'. The shorter the time of contacting; the better, particularly at the higher temperatures. It is preferred to operate at a temperature between about 10 C. and +10" C. and for a time of contacting of not more than about 20 minutes. The time of contacting in this embodiment in extractor is 15 minutes.

The feed may be introduced at various. points along the height of extractor 15. However, in this embodiment, all the feed is introduced at a point just below the vertical mid-point of extractor 15.

At an upper point of extractor 15, liquid HF from source 19 and BFS from source 21 are passed by way of lines 22 and 23 respectively, into line 24 and therefrom into extractor 15.

The contacting is carried out under substantially anhydrous conditions and the liquid HF contains not more than about 3% of water. In this embodiment, commercial grade anhydrous liquid HF is used.

Suicient liquid HF must be used to exceed the solubility thereof in the hydrocarbons and also to participate in the formation of a complex along with BF3 and the xylenes in the feed. In general, between about 5 and about 50 moles of liquid HF are used per mole of mxylene in extractor 15. More usually the usage of liquid HF is between about 7 and 15 moles. In this embodiment, 11 moles of liquid HF are used per mole of m-xylene in extractor 15.

It is known that BF3 and H F combine with xylene to form complexes having different stabilities. The complex of m-xylene is the most stable. By adjusting the amount of BF3, it is possible to separate m-xylene from o-xylene and p-xylene. The m-xylene appears in the HF-BF3 acid phase and the o-xylene and p-xylene appear as a ranate phase. By the use of countercurrent contacting in a tower providing about 5 theoretical stages, it is possible to separate a mixture of xylene isomers into an acid phase containing m-xylene and substantially no o-xylene and p-xylene and a ranate phase containing o-xylene, p-xylene, and maybe some m-Xylene (dependent on the BF3 usage). In order to accomplish the separation with minimum loss of o-xylene and pxylene to the acid phase, the BF3 usage is adjusted to about l mole per mole of m-xylene present in extractor 15.

The ethylbenzene present is very rapidly disproportionated to diethylbenzene and benzene and also may interact with xylene to form ethylxylene. The dethylbenzene and ethylxylene form stable complexes with HF and BF3 and in order to permit good separation of the xylene isomers, it is necessary to provide additional BF3 for thel complexing of any diethylbenzene and ethylxylene formed. Therefore, in addition to the about l mole of BF3 per mole of m-Xylene present, not more than about 0.5 mole of BF3 may be introduced per mole of ethylbenzene present in extractor 15. In this embodiment, the BF3 usage is l mole per mole of m-xylene and 0.2 mole per mole of ethylbenzene, in order to decrease the amount of ethylbenzene disproportionated.

In order to improve the degree of separation, a reux stream of high purity m-xylene from source 26 is introduced by way of valved line 27 into extractor 15 at a point. somewhat above the exit point for the acid phase. The amount of m-xylene refluxed will vary with the con- Cil ditions of operation in extractor 15. In this embodiment, about 3 moles of m-xylene are refluxed per mole of mxylene in the feed.

A raiinate phase comprising benzene, o-xylene, pxylene, ethylbenzene and pentane is withdrawn from the top of extractor 15 by way of line 29 and is introduced by way of line 30 into fractionator 31. Fractionator 31 is shown schematically and is provided with an internal reboiler 32. The temperature in fractionator 31 is so adjusted that HF and BFS occluded in the raffinate phase are removed overhead and are recycled to extractor 15 by way of line 33 and other lines not shown. Pentane diluent is withdrawn by Way of line 36 and recycled to extractor 15 by lines not shown. Benzene produced by the disproportionation (and interaction) is withdrawn by way of line 37 and is sent to storage not shown.

The bottoms fraction produced in fractionator 31 consists of essentially all of the o-xylene and p-xylene and about 75% of the ethylbenzene in the feed from source l0. This fraction is withdrawn by way of line 3S and is passed by way of line 39 into fractionator 4t?, which is provided with reboiler 41. Fractionator 40 is so designed that an o-xylene bottoms product of about 99% purity is obtained; the o-xylene is withdrawn by way of line 43 and sent to storage not shown. ln this operation, on o-xylene yield of on o-xylene charged to fractionator 40 is obtained.

An overhead fraction is withdrawn by way of line 46 and is passed through heat exchanger means not shown where it is cooled to operating temperature and is passed into crystallizer 51. The charge from line 46 is approximately o-xylene, 11%; p-xylene, 39%, and ethylbenzene, 50%.

Crystallizer 51 represents schematically a vessel or vessels for separating crystals of p-xylene from a mother liquor. Any of the conventional types of crystallizers may be utilized herein. Crystallizer 51 is operated at a temperature sulciently low to crystallize out only p-xylene, i. e., essentially pure p-xylene. The exact temperature of operation will be determined by the type of feed to crystallizer 51 and the amount of p-Xylene which is desired to be separated out. In general, the temperaturey of operation in crystallizer 51 is between about 15 C. and about -70 C. In this embodiment, the temperature of operation of crystallizer 51 is 65 C.

Crystals of p-xylene are withdrawn from the bottom4 of crystallizer 51 by way of line 52 and passed to centrifuge 54 wherein mother liquor is separated from the crystals. Other methods of separating mother liquor and crystals may be utilized.

Mother liquor is withdrawn from centrifuge 54 by way of valved line 56. This mother liquor has the approximate composition, o-xylene, 18%; p-xylene, 6%, and ethylbenzene, 76%. In order to maintain the slurry in crystallizer 51 at between about 20 and 40% of the contents, a portion of the mother liquor from line 56 is recycled by way of valved line 57 into crystallizer 51.

The purity of the p-Xylene is improved by washing the crystals with pentane, which is introduced from source 61 by way of lines 62 and 63 into centrifuge 54. The pentane washings are removed by way of line 64 and recycled to line 30 for charge to fractionator 31. Other methods of washing the crystals maybe used.

Essentially pure p-xylene crystals covered with pentane are withdrawn from centrifuge 54 by way of line 67 and passed to fractionator 68, provided with reboiler 69. Pentane is removed and recycled by lines 71 and 63. Pure p-xylene is passed to storage by line 72.

The mother liquor not required for recycle is passed by way of line 56 into fractionator 76 which is provided with reboiler 77. In fractionator 76, an ethylbenzene concentrate product containing about ethylbenzene and about 10% p-xylene is taken overhead. This high purity ethylbenzene product is passed to storage by way of line 78. In fractionator 76, about 90% of the ethylprocess.

benzene charged and about 50% of the p-xylene charged are taken overhead. A bottoms fraction consisting principally of o-xylene is withdrawn and recycled by way of lines '79 and 39 to fractionator 40.

The acid phase is Withdrawn from extractor 1S by Way of line 89 and is introduced into reactor 91. Reactor 91 is a vessel provided with motor driven agitator 92 and heat exchanger means 93 and 94. In reactor 91 the materials are contacted at a temperature and time relationship such that essentially all the ethylbenzenes interact with xylene to form l,3-dmethyl-S-ethylbenzene and any o-xylene and p-xylene present isomerize to rnxylene. In general, the temperature in reactor 91 is maintained between about C. and +175 C. Preferably the temperature is between about 30 C. and about 75 C. and the time of contacting is between about 15 minutes and about 6 hours wherein the longer times correspond to the lower temperatures. In this embodiment, the temperature in reactor 91 is 75 C. and the time is l5 minutes.

Material is withdrawn from an upper point of reactor 91 and is passed by way of line 96 into decomposer 101. Decomposer 101 is provided with internal heat exchanger 102. Decomposer 101 is a vessel adapted for quickly removing HF and BF3 from the acid phase.

The HF and BF3 must be removed under conditions of time and temperature such that no disproportionation of the m-xylene to trimethylbenzenes occurs. A suitable temperature is 50 C. HF and BF3 are taken overhead by way of line 104 and are recycled for reuse in the A pentane fraction is shown as being removed overhead by way of line 106 and is recycled for reuse in the process.

The reaction product mixture produced in reactor 91 is recovered as a bottoms fraction from decomposer 101. This reaction product mixture consists of benzene, mxylene, and 1,3-dirnethyl 5 ethylbenzene (1,3,5ethyl xylene). The reaction product mixture is removed from decomposer 101 by way of line 109 and is passed into fractionator111; a reboiler 112 is provided in fractionA ator 111. There is shown schematically as being withdrawn from fractionator 111 a benzene fraction by Way of line 116, m-xylene fraction by way of line 117, and a 1,3,5-ethylxylene fraction by Way of line 119.

In this illustrative embodiment, the C8 feed is separated into the following essentially pure product fractions, except for the ethybenzene which is 90% purity.

1 Based on ethylbenzene'n the feed.

Should the demand for l,3-dimethyl-5-ethylbenzene increase beyond that obtainable from the feed from source 11, additional m-xylene may be converted to the desired 1,3-dimethyl-5-ethylbenzene by introducing ethylene from source 121 by way of valved line 122 (shown dotted) into reactor 91.

In Figure 2 there is shown another method of carrying out the separation of the m-xylene from C8 aromatic hydrocarbons. In Figure 2, line 201 contains a rainate stream consisting of essentially pure o-xylene, p-xylene, and ethylbenzene derived by the procedure shown in extractor and fractionator 31 of Figure 1.

Material from line 201 and recycle material from other sources is passed by Way of line 202 into crystallizer 203. The remarks made with respect to crystallizer 51, in Figure 1, also apply to crystallizer 203. Crystallizer 203 is operated at a temperature 10W enough to crystallize not only p-xylene, but also o-xylene. In general, crystallizer 203 is operated at between about 50 C. and about 110 C. In this embodiment, the temperature is about C.

A mixture of crystals of o-xylene and p-xylene is withdrawn from the bottom of crystallizer 203 andis passed by way of line 204 into centrifuge 206. Other lmethods of separating crystals from mother liquors maybe utilized. Mother liquor is withdrawn by way of line 207.

In order to maintain the slurry in crystallizer 203 at between about 2,0% and 40% of the contents, a portion or the mother liquor in line 207 is recycled by way of valved line 209 to line 202. In this embodiment, the slurry is held at about 30%. The composition of the mother liquor in line 207 is approximately o-xylene, 10%; p-xylene, 3%; and ethylbenzene, 87%.

The mixture of o-xylene and p-xylene is passed from centrifuge 206 by way of line 211, heat exchanger 212 and line 213 into crystallizer 216. Herein the crystals have been melted and the liquid passed to crystallizer 216; however, the same result can be obtained by fractional melting methods. Crystallizer 216 is operated at about the freezing point of the eutectic mixture of o-xylene and p-xylene, i. e., about 35 C. The usual operating temperatures in crystallizer 216 are between about 30 C. and 35 C. In this embodiment, the temperature is 33 C.

The slurry from crystallizer 216 is passed by way of line 217 into centrifuge 21S. Essentially pure p-xylene crystals are separated and are sent by way of line 219 to storage. In this embodiment, about 70% of the p-xylene charged to crystallizer 216 are recovered per pass.

A second mother liquor is withdrawn from centrifuge 218 by way of line 221. Some mother liquor is recycled by way of valved line 222 into crystallizer 216 in order to maintain slurry conditions at between about 20% and 40%, preferably 30%.

The remaining mother liquor from line 221 is passed by way of line 226 into fractionator 227, which is provided with reboiler 228. Fractionator 227 is constructed and operated to produce a bottoms product containing 99{% of o-xylene. The o-xylene product fraction is withdrawn by line 229 and passed to storage not shown.

The overhead fraction from fractionator 227 contains about 75% p-xylene and maybe sold for p-xylene concentrate. Preferably this fraction is withdrawn by way of line 232 and is recycled either to crystallizer 203 by way of valved line 233 or to crystallizer 216 by way of valved line 234.

Mother liquor from line 207 is passed by way of line 241 into fractionator 242, which is provided with reboiler 243. Fractionator 242 is operated under conditions to take overhead by way of valved line 244 a high purity ethylbenzene product fraction containing in excess of 90% of ethylbcnzenethe remainder is p-xylene. About one-half of the p-xylene charged goes overhead. A bottoms fraction of o-xylene, p-xylene and ethylbenzeneabout 20% of the charge-is withdrawn as a bottoms fraction and is recycled to line 202 by way of lines 247 and 248. Or this stream may be recycled to fractionator 227 by way of lines 247 and 249.

In this mode of operation, the C8 feed is separated into the following essentially pure product fractions, except for the ethylbenzene which is in excess of 90% purity.

lBased on ethylbenzene In the feed.

Thus having described the invention, what is claimed 1. A process which comprises (1) contacting, under substantially anhydrous conditions (a) a feed containing o-xylene, m-Xylene, p-Xylene and ethylbenzene as essentially the only xylene boiling range hydrocarbon constituents and essentially no hydrocarbons reactive therewith, with (b) an HF BF3 treating agent consisting essentially of about 1 mole of BF3 per mole of mxylene plus not more than 0.5 mole of BF3 per mole of ethylbenzene and between about and 50 moles of liquid HF per mole of m-Xylene, at (c) a temperature between about 40 C. and -l-307 C. for a time between about 2 minutes and 30 minutes, to essentially avoid isomer ization of o-Xylene and p-Xylene, (2) separating a rafnate phase comprising benzene, o-Xyleue, p-xylene and ethylbenzene, from an extract phase comprising HF, EP3, m-xylene, C aromatic hydrocarbons and substantially no o-Xylene and p-xylene, (3) removing HF and B173 from said rainate phase to obtain a ramnate, (4) distilling said ranate under conditions to obtain a bottoms product consisting of high purity o-Xylene and a fraction consisting substantially of p-Xylene, o-xylene and ethylbenzene, (5) chilling said `fraction to a temperature between about C. and about 70 C., to produce essentially only crystals of p-Xylene, (6) removing mother liquor to obtain crystals of essentially pure p-xylene, (7) distilling said mother liquor under conditions to obtain a high purity ethylbenzene product fraction and a fraction containing substantially only o-xylene and p-xylene, and (8) removing HF and BF3 from said extract phase to recover a high purity m-xylene product.

2. The process of claim l wherein the mixed xylene fraction of step (7) is recycled to the distillative zone of step (4).

3. A process which comprises (1) contacting, under substantially anhydrous conditions (a) a feed containing o-Xylene, m-Xylene, p-Xylene and ethylbenzene as essentially the only Xylene boiling range hydrocarbon constituents and essentially no hydrocarbons reactive therewith,

with (b) an HF-BF3 treating agent consisting essentially of about 1 mole of BFS per mole of m-xylene plus not more than 0.5 moles of B133 per mole of ethylbenzene and between about 5 and 50 moles of liquid HF per mole of rn-Xylene, at (c) a temperature between about 40 C. and +30 C. for a time between about 2 minutes and 30 minutes, to essentially avoid isomerization of o-Xylene and p-xylene, (2) separating a ratlinate phase comprising benzene, o-xyiene, p-Xylene and ethylbenzene from an extract phase comprising HF, BF3, m-xylene, C10 arcmatic hydrocarbons and substantially no o-Xylene and p-Xylene, (3) removing HF and BF3 from said rainate phase to obtain a rainate, (4) chilling said raffinate to a temperature between about C. and about 110 C. to produce a mixture of crystals of p-Xylene and o-xylene, (5) separating said crystals from mother liquor, (6) recrystallizing said crystals at a temperature between 30 C. and 3 C. to obtain crystals of essentially pure p-xylene and a second mother liquor consisting essentially of about the eutectic mixture of o-Xylenc and p-xylene, (7) separating said p-xylene crystals from said second mother liquor, (8) distilling said second mother liquor to obtain an essentially pure o-Xylene fraction and a fraction consisting essentially of o-Xylene and p-Xylene, (9) distilling the mother liquor from step (5) to obtain a high purity ethylbenzene product and a fraction containing substantially only o-Xylene and p-Xylene and (l0) removing HF and BF3 from said extract phase to recover a high purity m-Xylene product.

4. The process of claim 3 wherein the fractions consisting essentially of o-Xylene and p-Xylene of steps (8) and (9) are cycled to a recrystallization zone.

References Cited in the le of this patent UNITED STATES PATENTS 2,511,711 Hetzner et al. June 13, 1950 2,528,892 Lien et al. NOV. 7, 1950 2,532,276 Birch Dec. 5, 1950 2,564,073 Lien et al. Aug. 14, 1951 2,667,446 Findlay Jan. 26, 1954 

1. A PROCESS WHICH COMPRISES (1) CONTACTING UNDER SUBSTANTIALLY ANDHYDROUS CONDITIONS (A) A FEED CONTAINING O-XYLENE, M-XYLENE, P-XYLENE AND ETHYLBENZENE AS ESSENTIALLY THE ONLY XYLENE BOILING RANGE HYDROCARBON CONSTITUENTS AND ESSENTIALLY NO HYDROCARBONS REACTIVE THEREWITH, WITH (B) AN HF-BF3 TREATING AGENT CONSISTING ESSENTIALLY OF ABOUT 1 MOLE OF BF3 PER MOLE ON M-XYLENE PLUS NOT MORE THAN 0.5 MOLE OF BF3 PER MOLE OF ETHYLBENZENE AND BETWEEN ABOUT 5 AND 50 MOLES OF LIQUID HF PER MOLE OF M-XYLENE AT (C) A TEMPERATURE BETWEEN ABOUT -40*C. AND +30*C. FOR A TIME BETWEEN ABOUT 2 MINUTES AND 30 MINUTES, TO ESSENTIALLY AVOID ISOMERIZATION OF O-XYLENE AND P-XYLENE, (2) SEPARATING A RAFFINATE PHASE COMPRISING BENZENE, O-XYLENE, P-XYLENE AND ETHYLBENZENE FROM AN EXTRACT PHASE COMPRISING HF, BF3, M-XYLENE, C10 AROMATIC HYDROCARBONS AND SUBSTANTIALLY 